A novel hexacyclic ring system from glycoluril

Mock, William L.; Manimaran, T.; Freeman, Wade A.; Kuksuk, Robert M.; Maggio, John E.; Williams, Dudley H.

doi:10.1021/jo00201a012

Cited by 22 publications

(14 citation statements)

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“…[21] Although theoretical studies by Pichierri, [22,23] have predicted that the sulfur analogs of CBs would be stable molecules with good binding properties to transition metal ions and metal surfaces, none of these analogs were achieved experimentally. [24] Similar attempts were reported by Heaven. [24] Similar attempts were reported by Heaven.…”

Section: Introductionsupporting

confidence: 65%

Hetero‐Bambusurils

Reany

Mohite

Keinan

2018

Israel Journal of Chemistry

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Synthetic anion carriers are essential for studying natural ion transporters and channels and for useful applications, such as treatment of channelopathies, supramolecular architecture, anion sensing and catalysis. Driven by the hypothesis that replacement of oxygen atoms in bambusurils (BUs) by other heteroatoms could significantly modify their anion binding properties, we calculated their molecular electrostatic potential and found a general trend of anion‐affinity: S>O>NH. We confirmed these predictions experimentally by synthesizing semithio‐ and semiaza‐BUs and studying their binding and transport properties. Although all analogs are excellent anion binders, only semithio‐bambus[6]uril is an effective transmembrane transporter capable of polarizing lipid membranes through selective anion uniport. Semiaza‐BUs exhibit simultaneous accommodation of three anions, linearly positioned along the main symmetry axis, which is reminiscent of natural chloride channels in E. coli.

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Section: Introductionsupporting

confidence: 65%

Hetero‐Bambusurils

Reany

Mohite

Keinan

2018

Israel Journal of Chemistry

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“…Aside from theoretical studies by Pichierri,8,9 which predicted interesting ligation to metal ions and metal surfaces, there has been only circumstantial evidence on attempts to prepare thiocucurbiturils. For example, shortly after his discovery of the cucurbituril structure, Mock reported the preparation of monothioglycoluril 10. Other attempts to prepare thioglycolurils probably reflect similar intentions 11…”

Section: Introductionmentioning

confidence: 99%

The Synthetic Challenge of Thioglycolurils

et al. 2014

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The very high stability of cucurbiturils under harsh acidic conditions and their reported prolific chemistry over more than three decades pose a question: why has no thiocucurbituril been reported to date? Furthermore, although glycoluril is a highly stable, easily accessible precursor of all cucurbiturils, its sulfur analog represents a yet unmet synthetic challenge. The reaction between glyoxal and thiourea was found to stop at the level of dihydroxyimidazolidine‐2‐thione, which is quite unstable under various acidic conditions. In an attempt to answer these questions, several stable analogs of thioglycoluril, that is, monothioglycoluril, ditolylthioglycoluril, and its diether derivative were prepared and characterized in the hope that they could be employed as building blocks for the synthesis of thiocucurbiturils. Several side products were also obtained that highlight the complex reactivity of thiourea in these reactions. The crystal structures of the above‐mentioned thioglycolurils are dominated by networks of hydrogen‐bonding interactions. Attempts to co‐oligomerize these compounds with formaldehyde clearly suggest that it is impossible to synthesize thiocucurbiturils by the methods commonly used for the preparation of cucurbiturils. Given that thiocucurbiturils are expected to be stable molecules, alternative synthetic strategies that are different from the thermodynamically controlled approaches must be designed.

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“…3a,6a-Diamino glycoluril has been analysed by Modric et al [6]. Derivatives containing nitro groups [7], methylene groups at the nitrogen atoms [8,9], and polycyclic rings [10] are known from the literature. Owing to the structural similarity, the chemical properties have been compared with the vitamin biotin [11].…”

Section: Introductionmentioning

confidence: 99%

“…Kim et al succeeded in preparing cucurbit [5][6][7][8]urils isolated from the condensation reaction of glycoluril and formaldehyde [18,19]. Day and Arnold investigated the reaction parameters for the synthesis of cucurbit [5][6][7][8][9][10][11]urils [20]. The syntheses Downloaded by [The University of Manchester Library] at 06: 24 25 November 2014 Glycoluril derivatives 45 of cyclohexyl cucurbit [5,6]uril [21] and diphenyl cucurbit [6]uril have also been reported [22].…”

Section: Introductionmentioning

confidence: 99%

Glycoluril derivatives as precursors in the preparation of substituted cucurbit[n]urils

Jansen¹,

Wego²,

Buschmann³

et al. 2003

Designed Monomers and Polymers

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Substituted glycolurils are of considerable interest for the synthesis of cucurbit[n]uriltype macrocyclic receptors. Thus, the present work investigates the formation and characterization of tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)dione (D glycoluril) and its derivatives. Acidcatalysed condensation reactions of these substances with formaldehyde lead to different products, depending on the reaction conditions chosen. Tetracyclic diethers are formed at low temperatures and long reaction times. Oligomeric chains are produced at temperatures higher than 50 ± C. Chains of suitable length are able to close in a cyclocondensation reaction under the formation of macrocyclic compounds of the cucurbit[n]uril type.

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A novel hexacyclic ring system from glycoluril

Cited by 22 publications

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Hetero‐Bambusurils

Hetero‐Bambusurils

The Synthetic Challenge of Thioglycolurils

Glycoluril derivatives as precursors in the preparation of substituted cucurbit[n]urils

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